Advanced Trouble on the Double
by SparkingSpirit
Summary: A simple play date between Ash and May becomes something much more when Team Rocket kidnaps the two of them. What will happen, and will they ever escape?


NOTE: This takes place YEARS after the Advanced series, Ash and May just scheduled a play date. Also, Ash is wearing his AG/BF outfit, May is wearing her Emerald outfit.

Ash was in front of the Pokemon Center, waiting for May to finish healing her Pokemon. Her Glaceon had bedazzled yet another newbie coordinator. The actual match was quite boring, because May more or less curbstomped the rookie. But then again, what else could he expect from a Top Coordinator?

"Ash! I'm done!" It was May, excited for some alone time with Ash. "I rented a room for us for a night, too!"

"That's great!" Ash smiled at her lovingly, not having expected this. "Tomorrow, we can see how Brock's doing! Say, how's Max?"

"He's fine, I suppose," May began. "But he's just so far away..."

"May, I'm sure nothing'll happen to him. He's perfectly capable on his own!" Ash put a hand on her shoulder. She seemed to perk up a bit as they went back inside of the Pokemon Center. Just as they had entered, white smoke formed all around the building, causing everyone to cough. The lights and electricity immediately stopped working afterwards.

"What was _that!?_" May gasped.

"Pikachu - use - Flash!" Ash said between coughs. His starter's Pokemon zigzag tail lit up in a yellow flash, brightening the area around them a little. The smoke started to fizzle out, revealing three shadowed figures.

"W-Who are you guys?" Ash heard Nurse Joy ask, but they simply laughed.

"Don't tell me, its them..." The boy groaned. May groaned with him.

"Don't you three ever give up!?" she yelled angrily.

"'Give up'? A foolish question indeed!" the old bitch began.

"You kinda walked right into that one," Ash whispered to no one in particular.

"The answer to come as we feel the need!" continued the man with the somewhat flamboyant voice.

"Bringing the blinding white light of evil into the future!"

"Thrusting the hammer of justice down onto the black darkness of the universe!"

"And carving our names into the rock of eternity!"

"The fiery destroyer, Jessie!"

"And with thunderous emotion, I am James!"

"Wisest of the wise, Meowth!"

"Now gather, under the name of Team Rocket!" the three of them finished together.

May immediately threw her Poke Ball. It was a good thing she healed her Pokemon before they came in. "Wartortle, on stage!" Her Wartortle was released in sprinkles and bubbles. "Bubblebeam!"

James tossed one of his own. "Yamask, Will-o-Wisp!" The ghost type released blue flames which collided with the bubbles, creating steam that blocked their vision.

"Woobat, Gust!" Ash heard Jessie command, but before he could do anything about it, the steam was all blown towards them, fogging up their sight even more.

"Ash, help!" May shouted from above. Ash quickly got Unfezant to blow the steam away, only to find May gone.

"May!" he cried, but Jessie got in front of him, and then kicked him below the belt, temporarily disabling him. Pikachu rushed in front of him to defend, but Meowth's charm flashed, blinding him. Pikachu's electricity flailed wildly, nearly hitting Ash.

"Pikachu!" Ash gasped, before a large net was thrown over him and Pikachu.

"How do you like our world wide web?" James sneered, before electricity coursed through the net, shocking Ash and Pikachu. That was the last thing he remembered before he blacked out.

xxx

"Very good work," a menacing voice boomed in his ears. "You've essentially disarmed the boy who's caused us trouble for many years." Ash slowly opened his eyes to see a middle-aged man in a suit. It was Giovanni. How had he ended up here? Where was he? He looked down, slightly relieved that he at least wasn't in the web anymore.

"What do you want with me? Where's May!?" he demanded.

"Silence, boy. Jessie, James, Meowth, take them to Dr. Zager. He'll see to it that they're no longer of any threat." Giovanni sipped a glass of wine as the trio yanked Ash out of the room. He struggled to get out of their grips, but his body was still weakened from that last electric shock.

"You're not going to get away with this! Whatever it takes, I will..." Ash began, but Jessie smacked him across the face. They then opened a door to see an old man with a monocle stepping out of the room. He briefly turned to them.

"So you got him after all. What did I tell you? For Team Rocket, nothing is impossible!" he exclaimed, before continuing on his path. They then walked into the room to reveal a purple-haired girl doing some paperwork.

"Dr. Zager is quite busy, as you can see," she said, not even looking up. She then pressed a button on her desk, and Pikachu was captured in an electric proof glass container.

"Pikachu!" Ash yelled, as a hole formed in the ground below it, where it fell. Ash tried to jump into the hole after it, but Seviper wrapped itself around it, constricting it.

"A-Ash! Pikachu!" May's voice cried from the left, as Seviper slammed him to the ground.

"If you two ever want to see Pikachu again, and also get out alive," the woman finally looked up at him. She was revealed to have glasses, as well as a maroon and black shirt with yellow buttons barely containing her bust. "You will do whatever I say."

Ash glared at her, before reaching for a Poke Ball. "No way! Squirtle, I - " His hand felt nothing on his belt. "...don't choose you..."

"Did you think we wouldn't take all of your Pokemon from you?" The woman got up and approached him, a whip in her hand.

"What do you want from me!?" Ash cried out, as she put her hand on his chin and tilted his head up.

She ignored his question and turned to the trio. "You three are dismissed until further notice. I'll deal with them." They walked away, with Jessie blowing a kiss to Ash. "As for you...strip."

Ash blinked. Had the secretary of Giovanni, the boss of Team Rocket, really just requested for him to strip, of all things? "You heard right. Strip. _Now_." She watched as Ash slowly unfastened his jacket. Impatient, she yanked his jacket and shirt off for him, revealing his hard abs. She then forced his footwear off, followed by his pants. He now only had on his hat and boxers. May was getting turned on just watching this. She tried to stifle her moans as the secretary rested her hand on Ash's crotch area. She was only touching through his boxers, but he would be lying if he said he wasn't turned on either way.

Ash bit his tongue, not willing to give in to her touch. She looked hot, but he would come on his own accord, not when she demanded it. He tried to focus on something else. He stared at May, who blushed under his gaze, but that just made him all the more hard. The secretary then gripped his shaft harder and began to stroke it up and down, while running her index finger through the head, preventing most of his precum from leaking. She knelt down to him while still running her hand through his cock, before turning to May.

"You. Come." Right as she turned back to him, her face now inches away from him, he began to release a little more cum. With an annoyed look on her face, the secretary applied more pressure with her finger on the head of his dick. "I wasn't talking to you."

Ash let out another moan he didn't even know he was holding. What was it about this woman that turned him on so much? May was now next to the two of them, her right hand twitching on her inner thigh.

"Let me...cum..." Ash begged, but the older woman simply reached into his boxers with her free hand and slapped his bare ass.

"Say 'please', and I might," she smirked, loving the look on Ash's face. He looked so needy, yet helpless to get what he wanted. He really was at her mercy...after Team Rocket had been at his mercy for years, it was quite ironic.

"...Please let me cum!" he yelled louder, glancing at May. By now, she was so turned on that she was fingering herself hard.

The secretary slowly glided her finger away from his cock, before then flicking it. Almost immediately after, she yanked his boxers off and tied some sort of ring around his shaft.

"B-But you said you'd let me cum!" Ash complained.

The woman flicked her tongue on it a few times, before looking up with a seductive smile. "I did say 'maybe', didn't I?" She then slapped his ass again as he held on to her and humped her knee in pleasure.

As much as she wanted to let him be, she had a reputation to uphold. She grabbed his balls and forced him off. "No touching."

Ash doubled over in pain as he rolled over. The lady left the room for a while as May nursed him. After a few minutes, he put his clothes back on.

"Come on, May, let's find our Pokemon and get outta here!" he yelled, barely managing to get his pants over the ring around his cock.

"But Ash, what if they find us?" May asked nervously, though Ash couldn't really blame her. Without her Pokemon, she was basically a sitting Psyduck.

Ash didn't answer, gesturing towards the door. He looked into the hallways to see who was there. To his surprise, the coast was completely clear, except for a few unattentive Rocket Grunts. Ash and May got ready to make their escape...


End file.
